Ammonia → HCID 12010693, compound

HRID 378780Notes

Reaction equation

HRID 378780 reaction equation
[Br:1][C:2]1[C:3]([C:11](N)=[O:12])=[N:4][C:5]([Br:10])=[C:6](Br)[C:7]=1Br.[NH3:14].C[OH:16]>>[NH2:14][C:7]1[CH:6]=[C:5]([Br:10])[N:4]=[C:3]([C:11]([OH:12])=[O:16])[C:2]=1[Br:1]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 21696642HCID 21696642, compound

Product 1

HCID 12010693HCID 12010693, compound

Procedure

3,4,5,6-Tetrabromopyridine-2-carboxamide (5.0 g) was selectively aminated with ammonia gas at RT in 100 mL methanol. The resultant solution was concentrated to an off-white solid and hydrolyzed with conc. sulfuric acid (25 mL) at 140° C. for 3 hr. the mixture was made basic with NaOH, extracted with EtOAc (2×100 mL), acidified and filtered to give 1.4 g of pure 4-amino-3,6-dibromopyridine-2-carboxylic acid; mp 205° C. dec.

Workup

  1. concentrationThe resultant solution was concentrated to an off-white solid and hydrolyzed with conc. sulfuric acid (25 mL) at 140° C. for 3 hr
  2. extractionextracted with EtOAc (2×100 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-fb557ee8ce70414a8c0f135b631c4c2d
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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